Anthony Tsakalos, an attorney in Goodwin’s Business Law Department and a member of the firm’s Real Estate Industry group, has over seven years of experience representing clients in all aspects of real estate law in Massachusetts, including: acquisitions and dispositions of real estate, the representation of lenders and borrowers in real estate and asset-based financing transactions, general real estate litigation matters, and commercial leasing and landlord/tenant matters, including the representation of numerous residential and commercial landlords in leasing transactions and summary process litigation in various courts throughout Massachusetts.

Mr. Tsakalos joined Goodwin in 2019 and focuses his practice on the representation of commercial developers, landlords, tenants, and lenders with respect to commercial leasing transactions.

Areas of Practice
Domaines D’Expertise





Recent commercial financing transactions:

  • Represented a Boston developer of hotels in a $14 million acquisition and refinancing transaction.*
  • Represented a Massachusetts bank in a $3.69 million loan to a rapidly growing landscaping and property management business.*
  • Represented a Boston developer in a $3.65 million acquisition of a large multi-family apartment building in Boston, Massachusetts.*
  • Represented a Massachusetts bank in a $13 million loan to a multi-state promotor of youth sports tournaments.*
  • Represented Cape Cod commercial developer in $9.67 million interest rate swap refinancing transaction.*

Recent commercial leasing transactions:

  • Represented New York-based development group in leasing additional 30,000 square foot of space to tenant on Madison Avenue, New York.*
  • Represented Cape Cod developer in lease negotiations with the Advance Store Companies (Advance Auto Parts) for the construction and leasing of a new 7,000 square foot location in Sandwich, Massachusetts.*

*Denotes experience prior to joining Goodwin.

Professional Activities

Mr. Tsakalos is a member of the Boston Bar Association, the Massachusetts Bar Association and is also a licensed Massachusetts real estate broker.

Professional Experience

Prior to joining Goodwin, Mr. Tsakalos served as an Associate Attorney at Greenbaum, Nagel, Fisher & Paliotti, LLP, located in Boston, Massachusetts, where he represented clients in all aspects of real estate transactions and litigation. Prior to that role, Mr. Tsakalos served as an Associate Attorney at Anetakis Law LLC, also located in Boston, Massachusetts, and focused his practice on the representation of banks and commercial lending institutions in commercial financing transactions ranging between $1 million and $50 million.

Additionally, Mr. Tsakalos served as Vice President and General Counsel of Tsakalos Realty Trust, a commercial real estate development organization located on Cape Cod, Massachusetts, presently leasing approximately 200,000 square feet of space to a wide variety of retail, office and medical use tenants.

Mr. Tsakalos is also a former small business owner, as he was the franchisee of Subway® restaurant #60187, located in Forestdale, Massachusetts, from September 2013 to September 2015.

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J.D., 2011
Suffolk University Law School
B.A., 2008
Boston College


Lawrence District Court, Hon. Mark A. Sullivan, Associate Justice of the Massachusetts Trial Court



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